Crystallography Reports ( IF 0.6 ) Pub Date : 2022-04-19 , DOI: 10.1134/s1063774522020055 A. N. W. Kadafour 1 , M. D. Bala 1
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Abstract
Formation of the title Schiff base compound (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol, C17H12N2O3 (1) was achieved by the condensation of 2-hydroxy-1-naphthaldehyde and 3-nitroaniline and confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet–visible spectroscopy and single-crystal X-ray diffraction. Compound 1 belongs to the orthorhombic system, space group P212121 and has intramolecular hydrogen bonds O–H⋅⋅⋅N and N–H⋅⋅⋅O. X-ray data also revealed a resonance structure that contains the equilibrium of imine-phenol (OH)/keto-amine (NH) tautomers of 1. However, spectroscopic data in common solvents and Hirshfeld surface analysis showed the predominance of the OH tautomer over the NH form of the Schiff base in solution.
中文翻译：
(E)-1-(((3-硝基苯基)亚氨基)甲基)萘-2-醇的晶体结构
摘要
通过 2-羟基的缩合形成标题席夫碱化合物 (E)-1-(((3-硝基苯基)亚氨基)甲基)萘-2-醇，C 17 H 12 N 2 O 3 ( 1 ) -1-萘醛和3-硝基苯胺，并通过核磁共振光谱、红外光谱、紫外-可见光谱和单晶X射线衍射证实。化合物1属于斜方晶系，空间群P 2 1 2 1 2 1并且具有分子内氢键O-H⋅⋅⋅N和N-H⋅⋅⋅O。X 射线数据还揭示了包含 1 的亚胺-苯酚 (OH)/酮基-胺 (NH) 互变异构体的平衡的共振结构。然而，普通溶剂中的光谱数据和 Hirshfeld 表面分析表明，OH 互变异构体在溶液中的席夫碱的 NH 形式中占优势。
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